In the Ming and Qing Dynasties, the Grand Canal transportation stimulated the vitality of the settlements along the canal. It gave birth to many canal towns with unique regional and cultural characteristics. In the paper, the application of the literature research method, the history map analysis method, and the system analysis method, Linqing ancient city landscape features have been analyzed. Its wisdom in building human settlements has been excavated, through the analysis of ancient documents, the comparison of historical maps, as well as the ArcGIS map registration. Influenced by the change in the regional water system, canal transportation, and city functions, the change of ancient city sites was summarized into embryonic form, pre-canal period, and post-canal period. In the same way, the evolution of ancient city form can also be summarized into three stages. (1) The market town and the granary had been growing simultaneously across the Huitong River. (2) The granary and its surrounding areas had been built into the administrative center Zhuancheng. (3) The market town and surrounding area had been built into a commercial and residential center Tucheng, the ancient city form had been completed at the same time. The wisdom of ancient city construction was embodied in the process of urban growth and construction, which was based on the premise of maintaining water safety and integrated nature, society, culture, economy, science, technology, and other elements. It also combined the idea of urban construction with ancient China’s simple ecological consciousness, idyllic thinking, and gardening concepts. In the end, the law of the land selection, the situation of the water system combing, the rites and music of the city construction, and the poetic construction landscape are four aspects of representation.